HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Winnipeg

$103+ Cheap flights from Chicago (CHI) to Winnipeg (YWG)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/13. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YWG
Apr 29 — May 61
Tue 4/29
Tue 5/6
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Winnipeg with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Chicago to Winnipeg

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Winnipeg (YWG). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated April 24, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$199
(Kiwi.com)

One-way from

$103
(Kiwi.com)

Popular in

February

Cheapest in

January

Average price

$743

Good round-trip deal

$535 or less

Good one-way deal

$194 or less
Provider with most accurate pricing for Chicago (CHI)-Winnipeg flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Winnipeg flights.
Search Deals
From Chicago (CHI) to Winnipeg
Search Deals
One-way flight from Chicago (CHI) to Winnipeg
Search Deals
High demand for flights, 3% potential price rise
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($18 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2025
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Winnipeg.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Winnipeg.
Search Deals

Find flight deals from Chicago to Winnipeg

Cheapest flights from Chicago to Winnipeg
Explore the most affordable flight options available from Chicago to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 24, 2025.

This Kiwi.com deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/135:30 pmORD - YWG
1 stop15h 33mWestJet
Wed 6/118:30 amYWG - ORD
1 stop8h 14mWestJet
Deal found 4/23$199
This Kiwi.com deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/65:48 pmORD - YWG
1 stop22h 40mMultiple Airlines
Fri 5/98:30 amYWG - ORD
1 stop8h 14mMultiple Airlines
Deal found 4/22$222
This Delta deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/289:00 amORD - YWG
2 stops14h 25mDelta
Tue 6/38:30 amYWG - ORD
2 stops11h 51mDelta
Deal found 4/22$362
This Mytrip deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/235:50 pmMDW - YWG
2 stops16h 36mMultiple Airlines
Sun 5/256:30 amYWG - MDW
1 stop10h 24mMultiple Airlines
Deal found 4/23$382
This Mytrip deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/79:40 amMDW - YWG
2 stops13h 06mPorter Airlines
Sat 6/1411:45 amYWG - MDW
2 stops29h 09mPorter Airlines
Deal found 4/23$390
This Delta deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/79:20 amMDW - YWG
1 stop7h 25mDelta
Sat 6/1412:26 pmYWG - MDW
1 stop4h 46mDelta
Deal found 4/22$427
This Gotogate deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/71:02 pmORD - YWG
Nonstop2h 29mAir Canada
Sat 6/142:20 pmYWG - ORD
Nonstop2h 31mAir Canada
Deal found 4/23$441
This United Airlines deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/301:00 pmORD - YWG
Nonstop2h 24mUnited Airlines
Sun 11/95:15 amYWG - ORD
1 stop5h 43mUnited Airlines
Deal found 4/23$522
This Trip.com deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/139:20 amMDW - YWG
1 stop10h 48mWestJet
Wed 6/119:00 amYWG - MDW
1 stop12h 45mWestJet
Deal found 4/23$593

Cheapflights Fare Finder

Customize your flight search to find flights from Chicago to Winnipeg that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 24, 2025.
Use the filters below to find and compare flights from Chicago to Winnipeg that are best for you.

Fly from

Chicago

Fly to

Winnipeg

Route

Depart

Return

Price

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Tue 5/13

5:30 pm-9:03 am

1 stop15h 33m

Winnipeg

Wed 6/11

8:30 am-4:44 pm

1 stop8h 14m

$199

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Tue 5/6

5:48 pm-4:28 pm

1 stop22h 40m

Winnipeg

Fri 5/9

8:30 am-4:44 pm

1 stop8h 14m

$222

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 5/28

9:00 am-11:25 pm

2 stops14h 25m

Winnipeg

Tue 6/3

8:30 am-8:21 pm

2 stops11h 51m

$362

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 5/23

5:50 pm-10:26 am

2 stops16h 36m

Winnipeg

Sun 5/25

6:30 am-4:54 pm

1 stop10h 24m

$382

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Sat 6/7

9:40 am-10:46 pm

2 stops13h 06m

Winnipeg

Sat 6/14

11:45 am-4:54 pm

2 stops29h 09m

$390

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Sat 6/7

9:20 am-4:45 pm

1 stop7h 25m

Winnipeg

Sat 6/14

12:26 pm-5:12 pm

1 stop4h 46m

$427

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 6/7

1:02 pm-3:31 pm

Nonstop2h 29m

Winnipeg

Sat 6/14

2:20 pm-4:51 pm

Nonstop2h 31m

$441

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 5/31

7:10 am-1:09 pm

1 stop5h 59m

Winnipeg

Sat 5/31

4:25 pm-10:41 pm

1 stop6h 16m

$535

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 5/13

9:20 am-8:08 pm

1 stop10h 48m

Winnipeg

Wed 6/11

9:00 am-9:45 pm

1 stop12h 45m

$593

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Tue 5/13

5:30 pm-9:03 am

1 stop15h 33m

$103

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/22

Showing 1-10 of 17 results
1
2

Compare providers for flights from Chicago to Winnipeg

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Winnipeg in April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Winnipeg flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Winnipeg flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Winnipeg flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Winnipeg flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Winnipeg flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Chicago to Winnipeg

Have a flexible travel schedule? Discover the best time to fly to Winnipeg from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Winnipeg

What is the cheapest month to book a flight from Chicago to Winnipeg?

Currently, August is the cheapest month in which you can book a flight from Chicago to Winnipeg (average of $358). Flying from Chicago to Winnipeg in April is currently the most expensive (average of $506). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to YWG?

Find hourly flight availability from Chicago to Winnipeg. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 24, 2025.

One of the essential ways to save on airfare from Chicago to Winnipeg is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight in the evening could potentially save you up to 12% on airfare.

Weekly flight availability from Chicago to Winnipeg

Explore weekly flight availability from Chicago to Winnipeg. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated April 24, 2025.

The most flights from CHI to YWG are scheduled on a Monday (3 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (3 on average).

Rainfall in Winnipeg by month

Plan your trip to Winnipeg by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Winnipeg ranges from 0.8 - 3.1 inches per month. June is typically the wettest month, when rainfall can reach 3.1 in. January is typically the driest time to visit Winnipeg when rainfall is around 0.8 in.

Temperature in Winnipeg by month

Plan your trip to Winnipeg by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Winnipeg, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 68.0 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 3.2 F).

Reviews of airlines servicing Winnipeg

Get insights into the airlines that provide service to Winnipeg. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Winnipeg. Reviews last updated April 24, 2025.
See what other customers who have flown with Porter Airlines, Delta and United Airlines from Chicago to Winnipeg have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
284 reviews

Overall

8.0

Boarding

8.2

Comfort

8.1

Crew

8.8

Entertainment

7.0

Food

7.6

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Porter Airlines
8.0
Very good
284 reviews
Porter Airlines
8.0
Very good
284 reviews

Overall

8.0

Boarding

8.2

Comfort

8.1

Crew

8.8

Entertainment

7.0

Food

7.6

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Delta
8.0
Very good
7,920 reviews
Porter Airlines
8.0
Very good
284 reviews

Overall

8.0

Boarding

8.2

Comfort

8.1

Crew

8.8

Entertainment

7.0

Food

7.6

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
United Airlines
7.4
Good
8,685 reviews
Porter Airlines
8.0
Very good
284 reviews

Overall

8.0

Boarding

8.2

Comfort

8.1

Crew

8.8

Entertainment

7.0

Food

7.6

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
WestJet
7.2
Good
2,816 reviews
Porter Airlines
8.0
Very good
284 reviews

Overall

8.0

Boarding

8.2

Comfort

8.1

Crew

8.8

Entertainment

7.0

Food

7.6

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Air Canada
7.0
Good
9,192 reviews
Porter Airlines
8.0
Very good
284 reviews

Overall

8.0

Boarding

8.2

Comfort

8.1

Crew

8.8

Entertainment

7.0

Food

7.6

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you

Related info for your journey

Find useful and relevant information for your journey from Chicago to Winnipeg. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Winnipeg from Chicago?

    Most people fly into Winnipeg (YWG) if they book a flight to Winnipeg from Chicago. On average, Winnipeg has 3 inbound flights from Chicago per day from 2 airlines. Winnipeg is conveniently located just 4.6 mi from Winnipeg’s city center.

  • What are the cheapest airlines flying from Chicago to Winnipeg round-trip?

    Flying on WestJet is currently your cheapest option to Winnipeg, with prices starting at $199. Additional round-trip tickets that might be worth considering are offered by Delta and Porter Airlines, with the lowest prices starting at $362 and $390, respectively. These flights start at 64% lower than the current average price 3 months from now.

  • What are the cheapest airlines to fly from Chicago to Winnipeg one-way?

    One-way options have recently been found by users for as low as $103 on WestJet. Other airlines that offer cheap prices include Porter Airlines from $147 and Delta from $184 one-way.

  • What are the most reliable airlines from Chicago to Winnipeg?

    The top 3 most reliable airlines when flying from Chicago to Winnipeg are SkyWest Airlines (89%), Air Canada (89%) and United Airlines (89%).

  • What are the cheapest flights from Chicago to Winnipeg?

    The cheapest flight price from Chicago to Winnipeg is $166. On average you can expect to pay $454. The most popular route, (Chicago O'Hare Intl - Winnipeg), can usually be booked for $222.

  • Can I find deals for flights from Chicago to Winnipeg that include hotel bookings?

    Yes. In addition to deals on Chicago to Winnipeg flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Winnipeg?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Winnipeg.

  • Can I find deals for business class flights from Chicago to Winnipeg?

    Yes. Cheapflights offers flight deals from Chicago to Winnipeg by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Winnipeg?

    Currently, August is the cheapest month in which you can book a flight from Chicago to Winnipeg (average of $358). Flying from Chicago to Winnipeg in April is currently the most expensive (average of $506). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Winnipeg

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Winnipeg flights
Midway to Winnipeg flights
St. Louis to Winnipeg flights

Top 2 airlines flying from Chicago to Winnipeg

Discover the top 2 airlines that operate flights from Chicago to Winnipeg. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$230Average$617FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$508Average$662FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.